Unlucky seven: the toughest Kentucky Derby beats

Profile Picture: Kellie Reilly

May 6th, 2016

Since the inaugural running of the Kentucky Derby (G1) in 1875, valiant winners have earned their turns in the spotlight. But there have also been heartbreaking losers in the Run for the Roses, and here’s my list of seven who suffered the toughest beats.

Proctor Knott (1889), the heavy favorite, did everything wrong before losing narrowly in a controversial finish. “A wild horse at the barrier” according to an old chart, Proctor Knott ran off prematurely prior to the actual start and nearly lost his jockey in “several spectacular lunges.” Once the race started in earnest, he was rank, and turning for home, he bolted to the outside fence. Meanwhile, Spokane hugged the inside rail down the stretch, and the two crossed the wire simultaneously across the width of the track. In these pre-photo finish days, the judges had to debate among themselves about who had won. “Opinion of the spectators was divided as to the outcome,” with Spokane and Proctor Knott partisans convinced their horse won. Spokane was declared the official winner, and a certain Frank James, brother of the infamous outlaw Jesse James, cashed a $5,000 win ticket on the 10-1 chance. But you’ve got to feel for Proctor Knott.

Blue Larkspur (1929) might appear a curious inclusion, since he was beaten more than six lengths in fourth behind Clyde Van Dusen. That Derby was contested in a sea of mud, however, and favored Blue Larkspur was not fitted with the right equipment – mud caulks – to help his footing. His trainer had been hospitalized, and neither his blacksmith nor his staff called an audible in the circumstances. Poor Blue Larkspur never got traction at Churchill Downs, but he went on to capture the Withers and Belmont en route to Horse of the Year honors, an influential stud career, and the Hall of Fame.

Brevity (1936) missed by a head as the 4-5 favorite after a troubled trip. The chart comment reads “probably best and knocked to his knees within a few strides after the start, had to race wide thereafter, closed resolutely and was wearing down the winner [Bold Venture].” Also unlucky in the 1936 Derby was Granville, who took a nosedive out of the gate and unseated his rider. Granville bounced back to reign as that season’s Horse of the Year and ultimately made the Hall of Fame.


Native Dancer (1953) suffered the only loss of his Hall of Fame career in this Derby, where he failed to catch front-running Dark Star by an agonizing head. A bump on the clubhouse turn set in motion a questionable trip, during which Native Dancer was taken, as one famous quip put it, “everywhere on the track but the ladies’ room.” This upset was an anomaly, for Native Dancer numbered the Preakness, Belmont, and Travers among his triumphs that season, and added the Metropolitan Mile at four. His subsequent influence on Derby pedigrees was incalculable.


Gallant Man (1957) endured perhaps the most brutal Derby beat of all, since he was the victim of pilot error as he was in the process of winning. He was lengthening stride and overtaking Iron Liege when his Hall of Fame jockey, Willie Shoemaker, misjudged the finish line and began to stand up in the irons. Although it took him only seconds to realize his mistake, the loss of momentum was too great for Gallant Man to overcome in so short a time. Gallant Man had the pleasure of dominating the Belmont in a then-American record for 1 1/2 miles, and collecting such prestigious trophies as the Travers, Jockey Club Gold Cup, Hollywood Gold Cup, and Metropolitan Mile. A botched Derby couldn’t keep this all-time great out of the Hall of Fame.


Sword Dancer (1959) and Tomy Lee each gave as good as they got in a stretch-long duel. Tomy Lee floated Sword Dancer out, Sword Dancer returned the favor by lugging in, and they scrimmaged to the wire. When Sword Dancer appeared to have the upper hand, they brushed again. That cost Sword Dancer more than Tomy Lee. Sword Dancer switched to his wrong lead (now leading with his left front rather than right front leg), losing forward momentum, while a galvanized Tomy Lee thrust his nose in front for Shoemaker at the wire. He also survived a claim of foul to keep his hard-fought victory. If only Sword Dancer could have stayed on his right lead in those final strides…


Cavonnier (1996) was inadvertently slapped in the face by a rival jockey’s whip as he rallied on the far turn, but withstood the affront and even overcame it. Getting through toward the inside, he rolled past the tiring leader Unbridled’s Song and appeared on his way to Derby glory. Then, wider out on the track, perhaps far enough away to be outside his field of vision, came Grindstone to mug Cavonnier at the wire. Cavonnier’s trainer, a newcomer to the Triple Crown scene, was heartsick after watching the Derby slip from his grasp. If he could have seen the future, he wouldn’t have felt so bad. That losing trainer was Bob Baffert, who’d go on to win four Derbies, most recently with Triple Crown star American Pharoah.